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Stereoselective Synthesis of Pyrrolidines Containing a 3‑Fluoro Quaternary Stereocenter via Copper(I)-Catalyzed Asymmetric 1,3-Dipolar Cycloaddition

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posted on 21.09.2017, 00:00 authored by Yang-Zi Liu, Shao-Jing Shang, Wu-Lin Yang, Xiaoyan Luo, Wei-Ping Deng
A highly efficient asymmetric 1,3-dipolar cycloaddition of azomethine ylides to β,β-disubstituted β-fluoroacrylates catalyzed by a chiral N,O-ligand/Cu­(CH3CN)4BF4 system is reported, affording chiral densely substituted pyrrolidines with four contiguous stereocenters, including one fluorinated quaternary stereocenter at the 3-position, in good to excellent yields (up to 99%), with excellent levels of diastereo- and enantioselectivities (dr >20:1; ee up to 99%).

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